Using 48 pieces from the Emmeline 4 Re (E4Re) upcycled collections from 2004-2009, an auto ethnographic review was conducted at product level. Seeking to understand and reflect on successes and pitfalls of the collections to draw insights into potential models and methods for design, for upcycling in the future. Working through pieces chronologically, observations were made based on material selection, design, manufacture and ease of sortation. Emmeline 4 Re was an upcycled fashion business spanning five years, 2004-2009. The business began as a Knowledge Transfer Partnership (KTP) scheme in collaboration with the Salvation Army Trading Company with a research aim ‘to develop and implement new manufacturing and marketing processes for the sales of novel fashion products from textile waste’. After the KTP the business then developed independently while still sourcing materials from SATCOL, the biggest collectors of waste textiles in the UK. The business had a concession in TOPSHOP’s flagship store in Oxford Circus, through boutiques nationally and internationally, and had one dedicated retail store in Princes Street W1. The paper reviews designs produced throughout this period and offers observations and recommendations to practitioners wanting to use upcycling as a sustainable design strategy.